9,10-Dibromoanthracene

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9,10-Dibromoanthracene
9,10-dibromoanthracene structure.png
Names
Preferred IUPAC name
9,10-Dibromoanthracene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.586 Edit this at Wikidata
EC Number
  • 208-342-4
UNII
  • InChI=1S/C14H8Br2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
    Key: BRUOAURMAFDGLP-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br
Properties
C14H8Br2
Molar mass 336.026 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H335, H410
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

9,10-Dibromoanthracene is an organic chemical compound containing anthracene with two bromine atoms substituted on its central ring. It is notable in that it was the first single molecule to have a chemical reaction observed by an atomic force microscope and scanning tunneling microscopy.[1]

Production[edit]

Ian M. Heilbron and John S. Heaton were the first to synthesize this in 1923 in England.[1]

Properties[edit]

9,10-Dibromoanthracene is electroluminescent, giving off a blue light.[2]

Reactions[edit]

The carbon–bromine bonds can be fragmented in two successive steps by voltage pulses from tip of a scanning tunneling microscope. The resulting carbon radicals are stabilized by the sodium chloride substrate on which the 9,10-dibromoanthracene reactant was placed. Further voltage pulses cause the diradical to convert to a diyne (or back again) via a Bergman cyclization reaction.[3]

Dibromoanthracene STM reaction.png

References[edit]

  1. ^ a b "9,10-Dibromoanthracene". American Chemical Society.
  2. ^ Brar, Sukhwinder Singh; Mahajan, Aman; Bedi, R. K. (10 January 2014). "Structural, optical and electrical characterization of hot wall grown 9,10-dibromoanthracene films for light emitting applications". Electronic Materials Letters. 10 (1): 199–204. doi:10.1007/s13391-013-3153-8. S2CID 135788635.
  3. ^ Borman, Stu (2016). "Chemists Nudge Molecule To React Then Watch Bonds Break And Form". Vol. 94, no. 5. p. 7.